1,3-dipolar cycloaddition of azides to alkynes

a dipolar cycloaddition and azide technology, applied in the direction of adhesives, etc., can solve the problems of incomplete polymerization and reduced yield, and achieve the effects of reducing the dsc peak temperature, and increasing the loading

Inactive Publication Date: 2010-05-13
HENKEL KGAA
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  • Application Information

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Benefits of technology

The patent text describes the results of a study on the effect of different catalysts on the curing temperature of a chemical reaction called azide/alkyne. The study found that adding a copper catalyst to the reaction reduced the temperature at which the reaction occurred. The study also found that adding a metal filler, such as silver flakes, to the reaction further reduced the temperature. This suggests that the copper catalyst and the metal filler work together to lower the curing temperature. The technical effect of this patent is to provide a method for controlling the curing temperature of the azide/alkyne reaction, which can be useful in various applications such as the production of optical components.

Problems solved by technology

The technical problem addressed in this patent is how to improve the efficiency and speed of an azide/alkyne chemical reaction while avoiding the drawbacks of current methods like slow curing times and limited effectiveness at low temperatures.

Method used

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  • 1,3-dipolar cycloaddition of azides to alkynes
  • 1,3-dipolar cycloaddition of azides to alkynes
  • 1,3-dipolar cycloaddition of azides to alkynes

Examples

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example 1

Curing Behavior of Azide and Alkyne Monomers in Bulk Phase without Catalysts

[0085]To get a better understanding of structure-cure temperature relationship, several structurally different alkynes were reacted in combination with dimer azide using DSC to react and cure the reactants. Tripropargylamine and nonadiyne were purchased from Aldrich; the other compounds were synthesized in-house. The results are reported in Table 1 and indicate that there is a strong dependence of cure temperature on the alkyne structure. All propargyl ethers, entries 1, 2, and 3, cured at 150° C. No significant effect of degree of branching of alkynes on cure temperature was observed (entries 1 and 2 compared to 3). In contrast to the propargyl ethers, the propargyl amines showed higher cure temperatures (entries 4 and 5). When the all-carbon alkyne, nonadiyne, was used, the cure temperature was the highest (entry 6).

[0086]The reactivity order of alkynes in the bulk phase uncatalyzed azide / alkyne chemistry ...

example 2

Catalytic Effect of Cu(I) Species in Bulk Phase Reactions

[0087]Three commercially available Cu(I) catalysts, CuI, CuSBu, and CuPF6(CH3CN)4, were screened to target a DSC peak temperature of approximately 100° C. compared to a control using no catalyst. The results are reported in Table 2. All of the catalysts used in the study decreased the DSC peak temperature of the formulations of entries 2, 3, 4, 10 compared to the control, entry 1; of the formulations of entries 6, 7 compared to the control, entry 5; the formulation of entry 9 compared to the control, entry 8. The magnitude of reduction in DSC peak temperature depended on the catalyst loading, entry 2 compared to entry 10, with higher loading giving the lowest peak temperature.

[0088]In addition to lowering the DSC peak temperatures, these Cu(I) catalysts also narrowed the cure profile considerably, making them more suitable for snap (fast) cure (see ΔT in entries 4, 6, 7, 9, compared with respective controls). With CuI and CuPF...

example 3

Effect of Cu(I) and Cu(II) Catalysts on Curing Temperature

[0089]Eight different Cu(I) catalysts and one Cu(II) catalyst without reducing agent were examined for their effect on the curing temperature of the azide / alkyne azide / alkyne chemistry using the same resin composition of dimer azide and bisphenol E propargyl ether in a 1:1 equivalent ratio with one weight % of the catalyst. Entry 1 is the control without catalyst, entries 2 to 9 are the Cu(I) catalysts, and entry 10 is the Cu(II) catalyst. Most Cu(I) catalysts significantly reduced the curing temperature (entries 2, 3, 4, 5, 6, 7), and some catalyzed the chemistry so dramatically that the resin composition gelled immediately after mixing at room temperature (entries 2 and 3, although no narrowing of DSC peaks were observed. The Cu(II) catalyst without a reducing agent unexpectedly also reduced the the curing temperature. The results are reported in TABLE 3.

TABLE 3EFFECT OF CU CATALYSTS ON CURING TEMPERATUREDSCTpeakTonsetΔTΔHE...

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Abstract

A process for the bulk polymerization, in the absence of any solvent, of a reactant containing azide functionality and a reactant containing a terminal alkyne functionality, in the presence of Cu (I) catalyst or in the presence of a Cu(II) catalyst without a reducing agent, is described. Polymerization can be achieved at temperatures less than 100° C., which is suitable for low temperature cures. A controlled synthesis for low molecular weight oligomers is disclosed.

Description

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Claims

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Application Information

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Owner HENKEL KGAA
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